Related Experiment Video
Updated: Sep 10, 2025

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
Published on: June 25, 2018
Aspartimide Formation and Its Prevention in Fmoc Chemistry Solid Phase Peptide Synthesis
Marco J W Kong1, Tim J H P van den Braak1, Kevin Neumann1
1Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, Nijmegen, 6525, AJ, Netherlands.
None:
Aspartimide formation remains a persistent challenge during Fmoc chemistry solid phase peptide synthesis. This review outlines various strategies to suppress base-mediated aspartimide formation, including the use of ester β-carboxyl protecting groups, non-ester-based β-carboxyl masking groups, and backbone-protecting groups. In addition, alternatives to the Fmoc group are explored that are cleavable under nonbasic conditions. The work discussed in this review highlights that the continued development of compatible and scalable tactics toward aspartimide prevention is essential for advancing peptide synthesis in both research and industry.
More Related Videos
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

